Triethylamine → Ethyl N-(ethyl carboxymethyl)oxamate
Reaction equation
C([NH:3][CH2:4][C:5]([OH:7])=[O:6])C.Cl.[CH2:9](N(CC)CC)[CH3:10].[CH2:16]([O:18][C:19](=[O:23])[C:20](Cl)=[O:21])[CH3:17]>ClCCCl>[CH2:9]([CH:4]([C:5]([OH:7])=[O:6])[NH:3][C:20](=[O:21])[C:19]([O:18][CH2:16][CH3:17])=[O:23])[CH3:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of ethyl glycine·HCl 2 (38.4 g, 275 mmol) in 1,2-dichloroethane (360 mL) was added triethylamine (77.0 mL, 550 mmol) at room temperature. After stirring for 30 minutes the heterogenous mixture was cooled to 0° C. and ethyl oxalyl chloride 1 (30.3 mL, 275 mol) was added dropwise over the course of 1 h. Upon completion of the addition, the cooling bath was removed and the reaction was stirred at room temperature overnight. The reaction was diluted with water (250 mL) and the layers separated. The aqueous layer was backwashed with 2 portions of dichloromethane (250 mL). The combined organic layers were washed with water (250 mL), followed by brine (250 mL), dried over MgSO4 and concentrated to give an oil 3 that was taken directly onto the next step.
Workup
- additionUpon completion of the addition
- customthe cooling bath was removed
- stirringthe reaction was stirred at room temperature overnight
- additionThe reaction was diluted with water (250 mL)
- customthe layers separated
- washThe combined organic layers were washed with water (250 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3261838be3f34ce08df745d2ec1cf0cd
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06462050B1
Reaction notes
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